Formaldehyde → HCID 178483376, compound

HRID 849407Notes

Reaction equation

HRID 849407 reaction equation
[ClH:1].Cl.N[CH2:4][CH:5]([N:11]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[CH2:15][N:14]([S:22]([CH3:25])(=[O:24])=[O:23])[C@H:13]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:12]1)[C:6]1[N:7]=[CH:8][NH:9][CH:10]=1.[C:33]([O-])(=O)C.[Na+].C=O.[BH3-][C:41]#[N:42].[Na+]>CO.C(O)(=O)C.C(OCC)(=O)C>[ClH:1].[ClH:1].[CH3:33][N:42]([CH3:41])[CH2:4][CH:5]([N:11]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[CH2:15][N:14]([S:22]([CH3:25])(=[O:23])=[O:24])[C@H:13]([CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:12]1)[C:6]1[N:7]=[CH:8][NH:9][CH:10]=1

Participants

8

Reactant 4

HCID 712Formaldehyde2×HCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydride2×HCID 178504915HCID 178504915, compound

Product 1

HCID 178483376HCID 178483376, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of the free base of Example 258 (20 mg) in methanol (1 mL) and acetic acid (0.5 mL) with sodium acetate (100 mg), was added 30 μL of formaldehyde (37% aq. solution), followed by NaCNBH3 (15 mg). The mixture was stirred for 15 min, additional formaldehyde (30 μL) and NaCNBH3 were added and the mixture was stirred for 30 min and diluted with ethyl acetate and quenched with 3 mL of NH4OH solution. The organic layer was separated, washed with 1 N NH4OH solution and brine, dried, and concentrated. The residue was converted to its HCl salt as described in Example 257 (23 mg). MS (M+H)+ 454.

Workup

  1. stirringthe mixture was stirred for 30 min
  2. customquenched with 3 mL of NH4OH solution
  3. customThe organic layer was separated
  4. washwashed with 1 N NH4OH solution and brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-15e8027169424a218e72e635674936dd
Source dataset
uspto-grants-2000_01
Patent number
US06011029

Reaction notes

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